Top Winter Vacations - Vacation Rentals in Upper Arsnicker Keys

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From US $1,313

         

10.0 (121 Reviews)

House

5 bedroom - Deep Dockage & Heated Pool in Islamorada.

• Air Conditioner
• Parking
• Pool

• Florida
• Islamorada

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From US $449

         

|

10.0 (1 Review)

House

Jewel in the Sea

• Air Conditioner
• Security/Safety
• Sports/Activities

• Florida
• Marathon

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From US $446

         

|

8.8 (62 Reviews)

Condo

Topsider Resort

• Air Conditioner
• Parking
• Pool

• Florida
• Islamorada

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From US $403

         

9.8 (174 Reviews)

Villa

DUPLEX IN DUCK KEY, 2 Bedroom/2 Bath, W/Private 90' Dock, Trailer Storage INCL

• Air Conditioner
• Parking
• Pool

• Florida
• Marathon

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From US $372

         

|

10.0 (1 Review)

Villa

Villa del Sol - 2-3 Villa - OS Slip Ramp Pkg

• Air Conditioner
• Parking
• View

• Florida
• Duck Key

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From US $639

         

|

10.0 (164 Reviews)

Hotel

The Caribbean Resort

• Air Conditioner
• Pool
• Wheelchair Accessible

• Florida
• Islamorada

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From US $403

         

9.8 (161 Reviews)

Villa

DUPLEX IN DUCK KEY, 2 Bedroom/2 Bath, W/Private 90' Dock, Trailer Storage

• Air Conditioner
• Parking
• Pool

• Florida
• Marathon

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From US $196

         

|

9.7 (3 Reviews)

Apartment

Harbor Villa

• Air Conditioner
• Wheelchair Accessible
• Balcony/Terrace

• Florida
• Marathon

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From US $570

         

|

9.4 (419 Reviews)

Hotel

Casa Morada

• Air Conditioner
• Parking
• Pool

• Florida
• Islamorada

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From US $513

         

10.0 (31 Reviews)

House

NEW POOL * Waterfront Paradise with Amazing Sunsets on Beach*

• Air Conditioner
• Parking
• Pool

• Florida
• Islamorada

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From US $528

         

9.8 (19 Reviews)

House

3200sqft Masterpiece Home, Fishing Paradise ,Waterfront, Beach, Pool, Islamorada

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Islamorada

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From US $1,836

         

10.0 (108 Reviews)

House

Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views

• Air Conditioner
• Parking
• Pool

• Florida
• Islamorada

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From US $107

         

7.4 (8 Reviews)

House

Outdoor Resorts, Long Key, FL

• Air Conditioner
• Parking
• Pool

• Long Key
• Layton

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From US $592

         

10.0 (1 Review)

House

ISLAMORADA BEACH HOUSE

• Air Conditioner
• Parking
• TV

• Florida
• Islamorada

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From US $469

         

10.0 (221 Reviews)

Condo

Renovated 2BR Villa with Spa, Water Views & Private Patio with Private Dip Pool!

• Air Conditioner
• Parking
• Pool

• Florida
• Marathon

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From US $570

         

10.0 (205 Reviews)

Condo

Luxury 3BR/3BA Cottage with the Best Sunset Views in the Florida Keys!

• Air Conditioner
• Parking
• Pool

• Florida
• Duck Key

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From US $438

         

10.0 (185 Reviews)

House

Best Deals in Duck Key . 2 Bedroom/2 Bath w/40' 'Dock, Trailer Storage Incl,

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Marathon

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From US $411

         

10.0 (172 Reviews)

Villa

DUPLEX IN DUCK KEY, 2 Bedroom/2 Bath w/40' Dock, Trailer Storage Incl.

• Air Conditioner
• Parking
• TV

• Florida
• Marathon

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From US $1,181

         

10.0 (160 Reviews)

House

Waterfront! 4 Bed/3 BA Townhome, 32FTDock, Cabana Club, Paddleboard, Beach Gear!

• Air Conditioner
• Parking
• Pool

• Florida
• Marathon

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From US $534

         

10.0 (157 Reviews)

House

DUPLEX IN DUCK KEY Grand 3/2 W/90' Private Dock, Trailer Storage included

• Air Conditioner
• Parking
• Pool

• Florida
• Marathon

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From US $445

         

10.0 (156 Reviews)

Condo

AQUAMARINE OCEANVIEW+”SPECIAL RATES”+nDOCK+POOL+GYM+SPA+”153”5 STAR REVIEWS!

• Air Conditioner
• Parking
• Pool

• Florida
• Islamorada

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From US $752

         

10.0 (92 Reviews)

House

TikiBar with TV &Stereo, PrivateSpa, Heated Pool, Hammock,SUP’s, Kayaks,Bikes,FP

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Islamorada

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From US $1,271

         

10.0 (88 Reviews)

House

Next availability Aug 15th 2026 - Booking 2027 Oceanfront - Heated Pool - Dock

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Islamorada

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From US $1,407

         

10.0 (77 Reviews)

House

Sunset Reef - Bayside Gated Estate, Pool, Spa, Deep Water Dock, Kayaks & SUPs

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Islamorada

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